Podcast Summary: Travis Makes Money

Episode: Make Money with Strategy Sprints, featuring Simon Severino
Host: Travis Chappell
Guest: Simon Severino
Date: February 27, 2026

Episode Overview

In this episode, Travis Chappell sits down with Simon Severino, celebrated business strategist, triathlete, author of Strategy Sprints, and CEO of Strategy Sprints. Together, they discuss tactical approaches to earning more money, building resilient income streams, the difference between making and keeping wealth, and the importance of designing a life you truly enjoy. Simon also shares his personal money philosophies, practical business frameworks, and the role of health in sustaining entrepreneurial success.

Key Discussion Points & Insights

Simon's Money Journey and Early Influences

• Background
  • Simon grew up in a family that valued education over money. He studied philosophy and initially lacked clear career direction.
    • “I was never excited about money and I didn’t make any money for a very, very long time. I grew up in a family that didn’t care about money. We cared about education, books. That was our thing.” (01:38 – Simon)
• Kickstarting His Career
  • Landed a job in strategy consulting due to his high academic achievements; quickly began to solve board-level business problems across global markets.
  • Fell in love with problem-solving for large organizations, gradually amassing a treasury of repeatable tools and templates.

The Birth and Growth of Strategy Sprints

• From Consulting to Entrepreneurship
  • Recognized the value of his toolbox across markets and industries; decided to go independent and package his knowledge into “Strategy Sprints”.
    • “I went on my own. I started Strategy Sprints… We have to share this with people. It became a book, Strategy Sprints: How to Run a Business in an Agile Way.” (04:50 – Simon)
  • Built not only one-on-one coaching, but cohort-based group coaching, and a 250-member community via their proprietary app.
• Helping Entrepreneurs
  • The community focuses half on building wealth (marketing and sales) and half on preserving wealth (investing and money management).
    • “It’s a very different skill to learn how to make money… but then it’s a very different skill to actually keep that money.” (06:25 – Simon)

The Philosophy of Wealth: Making vs. Keeping

• Defining Wealth
  • Echoing Scott Galloway’s insight: Wealth is not income but the gap between what you earn and what you keep.
  • Many with high income spend nearly as much as they earn—real wealth is created through managing this delta.

Agile: Adapting Quickly in Business

• Agility Defined
  • In business context, agility is the speed at which you can pivot or adapt to market changes.
    • “Can you turn direction quickly or not?... If your supply chain costs are going up by 15%, can you change your contractors in two days? That’s agile.” (08:19 – Simon)
• Agility Across Company Sizes
  • Agility is not exclusive to small businesses; large companies like Amazon can be highly agile due to their organizational structure.
    • “There are small rigid teams and there are large, very agile teams… It’s how you organize yourself.” (09:17 – Simon)

Building Multiple Income Streams: The 12 Money Systems

• Diversity for Resilience
  • Simon shares a detailed view of his personal income systems—advising his sprint clients to cultivate 5–7 at all times to boost resilience.
  • Key Systems: Consulting, cohort programs, licensing, royalties, paid newsletter, selling options, compounding income (stock picking), sponsorships, physical products, real estate, and more.
    • “Most people think that they have to pay for marketing. Not only you don't have to pay for marketing… I want to get paid for marketing… Most people never realize this is possible.” (15:46 – Simon)
  • Simon provides practical examples: newsletter subscribers converting to paid early on, licensing deals for international book translations, options trading portfolio made public to his community for learning.
    • “We started with $25k last January, now… that public portfolio is $170k. That’s the options income.” (19:30 – Simon)

Designing Your Ideal Life: Money as a Vehicle

• Structuring Life with Intention
  • Emphasizes starting with the way you want to experience your days, then building money systems to support that.
  • An “ideal day” consists of time for workouts, deep work, family, and meaningful interactions.
    • “That's what makes me happy, right? That's an ideal day. And I'm blessed that this is how my days look… This would be my day [even] if I was a billionaire.” (12:28 – Simon)
  • “The solve is not necessarily having the most money in my bank account... The solve is structuring my day in a way that is engineered thoughtfully by how I want to live my life. The money sort of takes care of itself at that point.” (14:00 – Travis)

The Critical Role of Health & Energy

• Athlete Mindset
  • Simon, a regular rower and weightlifter, sees daily workouts as vital for long-term energy, focus, and health.
    • “I have this body for probably, I don't know, 100 years in total… I just want to stay 40 as long as possible. That's why I work out every day.” (21:57 – Simon)

Upcoming Book: Time Freedom

• Co-Authored with Jay Abraham
  • Time Freedom focuses on the core reason entrepreneurs seek success: autonomy and meaningful use of their time.
  • Structured around three pillars:
    1. Simplify: Declutter your task list and focus on what matters.
    2. Multiply: Expand impact by creating scalable assets like group programs, international rights, or certifications.
    3. Compound: Learn to invest and grow wealth for sustained freedom.
    • “Each chapter helps you solve the problem that you wanted freedom in the first place… So the first three chapters, they help you simplify… The next four… are about multiplying… The last bits… are about compounding.” (23:45 – Simon)

Memorable Quotes

• On Wealth:
  • “It’s a very different skill to learn how to make money… but then it’s a very different skill to actually keep that money.” (06:25 – Simon)
• On Agility:
  • “Can you turn direction quickly or not?... That’s agile.” (08:19 – Simon)
• On Multiple Income Streams:
  • “Most people think that they have to pay for marketing. Not only you don't have to pay for marketing… I want to get paid for marketing.” (15:46 – Simon)
• On Lifestyle Design:
  • “That's what makes me happy, right? That's an ideal day. And I'm blessed that this is how my days look… This would be my day [even] if I was a billionaire.” (12:28 – Simon)
• On Health:
  • “I just want to stay 40 as long as possible. That's why I work out every day.” (21:57 – Simon)

Important Timestamps

• 00:30 – 01:28: Travis introduces Simon and his background/accomplishments.
• 01:31 – 04:50: Simon discusses growing up, studying philosophy, and finding a career in strategy consulting.
• 04:50 – 07:04: Building Strategy Sprints, starting to package and share his toolbox, and building a global, scalable community.
• 07:04 – 08:19: The difference between earning and keeping money; what true wealth is.
• 08:19 – 09:40: Agility in business—definition and examples.
• 11:02 – 12:28: Simon’s work/life integration and ideal daily routine.
• 14:54 – 17:57: Simon’s approach to multiple income streams, with specifics on consulting, licensing, royalties, paid newsletters, and options strategies.
• 21:33 – 22:40: The importance of health and exercise for entrepreneurs.
• 23:45 – 25:17: Summary of the book Time Freedom and the key frameworks inside.

Resources, Tools, and Where to Find Simon

• Strategy Sprints:
  • Website, free 7-day Sprint Club trial, coaching, tools and templates: strategysprints.com
  • Strategy Sprints (Book)
• Upcoming Book: Time Freedom (with Jay Abraham)
• Connect with Simon: Visit the website, download the app, or join the community for real-time advice and access to all 12 money systems.

This rich and practical episode is a blueprint for any entrepreneur looking to build autonomy, resilience, and wealth by working smarter—while building a life they actually want to live.